Sodium Carbonate → (E)-3-(1-{4-[2-(4-Methyl-piperazin-1-yl)-pyridin-4-yl]-benzenesulfonyl}-1H-pyrrol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1445496ノート

反応式

HRID 1445496 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[CH:37][N:36]=2)[CH2:31][CH2:30]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:28][N:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:40]=[C:39]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([N:11]4[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][O:23]5)=[O:19])=[CH:12]4)(=[O:10])=[O:9])=[CH:4][CH:3]=3)[CH:38]=[CH:37][N:36]=2)[CH2:33][CH2:34]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 86621691(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

生成物 1

HCID 86621699(E)-3-(1-{4-[2-(4-Methyl-piperazin-1-yl)-pyridin-4-yl]-benzenesulfonyl}-1H-pyrrol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide収率 64.3%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (6.8 g) and 1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-piperazine (5.0 g) are dissolved in DME (300 mL). Under an inert gas atmosphere are added (Ph3P)3PdCl2 (2.1 g) and 2M Na2CO3-solution (44 mL). The mixture is heated to 100° C. for 2.5 h. After filtration and extraction, the crude product from the organic phase is purified by silica gel flash chromatography. By means of chloroform/EtOH (30:1-19:1). 5.3 g of the title compound are obtained as brownish oil.

後処理

  1. filtrationAfter filtration and extraction
  2. customthe crude product from the organic phase is purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-b0c59daef0824a1b887f1c8bef755171
出典データセット
uspto-grants-2010_02
特許番号
US07666868B2

反応ノート

読み込み中…